


Bringing Up the Rear

by emani-writes (Thrsdynxt)



Series: SPN Poly BINGO 2017 [4]
Category: Supernatural
Genre: Anal Fingering, Anal Sex, Bondage, Cock Slapping, Come Swallowing, Continuation, Dirty Talk, Dom/sub Undertones, Dubious Consent, Face-Fucking, Felching, M/M, Mildly Dubious Consent, Multi, Oral Sex, Pirate Dean, Plot What Plot/Porn Without Plot, Rimming, Rough Sex, Sex, Spanking, Threesome - M/M/M, if by undertones I mean Dean being under everyone else in this fic, pirate Benny, ropes, stowaway cas
Language: English
Status: Completed
Published: 2017-01-25
Updated: 2017-01-25
Packaged: 2018-09-19 21:59:40
Rating: Explicit
Warnings: No Archive Warnings Apply
Chapters: 1
Words: 2,666
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/9461966
Author URL: https://archiveofourown.org/users/Thrsdynxt/pseuds/emani-writes
Summary: By popular demand, a scene immediately following up where my original pirate au (Earning His Keep) left off. Being the new Cabin Boy has it’s perks. Namely getting ridden hard and put away wet by Captain Dean and First Mate Benny.





	

**Author's Note:**

> I have been working on this scene for DAYS. I made a valiant try to just write the scene with no outline but, apparently, when I do it that way no one seems to know where to put their hands and Castiel at least ends up a little camera shy. ALSO! Apparently, I can foreplay to black with one eye closed and not even break a sweat EVEN IF THAT WASN’T MY ORIGINAL INTENT but the second penises start touching I become a blushing virgin. Guess that means I need more practice, yeah?
> 
> Feel free to read [Earning His Keep](http://archiveofourown.org/works/9385577) first (or not, you do you) and then come back here and tell me (preferably nicely because I'm a fragile little snowflake) if I lived up to the hype!
> 
> Written for SPN Poly BINGO 2017  
> Square filled: **Bed Sharing** (You might need to squint _just_ a little.)

Castiel tried valiantly to swallow down his nerves. The stew and ale he’d eaten sat heavy in his belly as First Mate Benny made sharp tugs and quick knots to the coarse rope securing his bound hands to the headboard of Captain Dean’s bed. His knees already ached from the lumpy mattress.

Glancing about, Castiel’s cheeks flamed when he caught sight of Captain Dean. The man was draped indolently across a deep red, plush-looking chair. His shirt and jacket had been removed revealing a flat, tattooed chest, and his loosely fisted hand was stroking languidly over his deep red cock. Glancing up, Castiel found the Captain watching him intently, a smirk planted firmly on his lips. Dean winked and Castiel groaned feeling his blush ignite down his chest. He squeezed his eyes tightly shut, pressing his face to the bicep of his right arm.

Behind him, Benny chuckled and Castiel tensed, starting in surprise when a warm, calloused hand caressed the swell of his ass. 

“Ain’t he pretty, Captain? All trussed up for us to use. Bet he’s gonna make the sweetest noises.”

Dean hummed his agreement, waving his hand for Benny to get on with it already.

 _Crack_! Castiel bucked forward, cursing at the sting across the back of his thigh. 

“There’s one,” Benny rumbled, hands gripping and squeezing at Castiel’s reddened flesh. “That’s right, boy. Sing for your Captain.”

Castiel whimpered and groaned, shivering with equal parts desire and pain as Benny landed strike after strike to his burning ass. Crying softly, Castiel fought to keep his face hidden between his arms, ashamed at just how hard and heavy he felt between his legs at the rough treatment.

“Now, now, darling,” Benny rumbled, big hands coming up to grasp Castiel’s hips, thumbs running in soothing circles . “None of that. I ain’t gonna really hurt ya.”

Soft lips caressed the base of his spine and Castiel arched, moaning.

“That’s it, pretty boy,” Benny whispered against his skin, dragging his coarse stubble down Castiel’s tender flesh. “Show the Captain how good you are.”

Castiel whined again, shuddering as rough hands pulled him wide. He pressed his hot face even harder into arm, self-consciousness, fear, and eagerness waring in his churning gut. Behind him, Benny hummed thoughtfully, squeezing the meat of his ass before leaning forward. 

The first teasing flick of Benny’s tongue sent Castiel wailing, lurching forward in surprise. Benny grunted, yanking Castiel back roughly and spearing him with his tongue. Castiel keened, kicking his feet at the overwhelming sensation. Benny pulled back, soothing his hands up Castiel’s naked back. 

“Calm down, boy. A little tonguing ain’t nothing to fret over.” Castiel glanced back over his shoulder, surprised to find Benny sitting up on the bed smiling kindly as he caressed his sore ass. “There’s a good boy,” he praised. “Let Benny make you feel good, darling.” Icy blue eyes bore intently into Castiel’s as Benny slowly eased his fingers down to brush teasingly over Castiel’s tight muscle. Castiel squeaked and tensed, hiding his face once again before slowly relaxing into Benny’s touch. Benny’s hand slid down further, gliding over Castiel’s balls and gripping his filling cock. Castiel moaned gutturally as Benny pumped his cock once, twice. 

“Atta boy,” he said, using his free hand to push down on Castiel’s back, causing him to arch his back and present his hole. Lips dragged along his hip edging ever closer to his exposed pucker. “Just relax now. I’mma open you up nice and slow.”

Castiel squeezed his eyes shut tight, keening loudly as Benny once more flicked his tongue teasingly over his hole, still holding tight to Castiel’s now aching cock to he couldn’t buck away. Benny set a slow, steady rhythm, pressing his tongue against the fluttering muscle, though not yet breaching the rim. What had been foreign and frightening before was now causing curls of desire to lance through Castiel’s belly and with a surprising sort of desperation, he found himself pressing back into Benny’s face. Castiel felt as the man behind him smirked when a begging whine burst from Castiel’s throat. Pulling back, Benny smacked a heavy hand down across Castiel’s ass, grabbing the cheek roughly, and giving it a jiggle. Benny released Castiel’s shaft only to wrap around the base of his cock and balls like a steel ring. 

Benny tugged, and Castiel groaned, panting harshly into the space between his arms. 

“Tha’s right. Let the Captain hear you.” Benny then laved his warm, wet tongue across Castiel’s balls, causing Castiel to gasp in surprise. A quick suck to the dark purple head had Castiel reeling. Benny hummed in delight, tonguing teasingly as Castiel’s weeping slit. 

“Mmm. Such a pretty little cock. You want the Captain to suck on your pretty cock while I open you wide?”

Shuffling to his left startled Castiel out of his sex hazed mind and he glanced toward Dean to see the man crawling to them as quickly as his knees allowed. Dean stopped only when his shoulder grazed Benny’s, bright green eyes staring mesmerized at Castiel’s fluttering, wet hole.

Slowly, Dean reached out one long finger to tease and pull at the rim. Dean groaned when Castiel’s muscle fluttered under his ministrations. 

“Holy.. fuck, Benny, yeah. Keep licking his ass. Make him wet and sloppy for me.” 

Benny chuckled and resumed his explorations, causing Castiel’s vision to blur. The sound of dragging across wooden boards jarred Castiel and he watched as Dean dipped his fingers into a pot of sweet-smelling oil, rubbing them together before gliding feather-light touches over Castiel’s full cock. Castiel shook in pleasure. He panted and moaned and keened as Dean gently, almost lazily, stroked him front root to tip, fingers occasionally dipping in to tease at Castiel’s foreskin. Then Benny added a finger.

“Yes! Oh, god, please, sir, please,” Castiel babbled, head thrown back, eyes squeezed tight.

Benny grunted, nodding his chin at Dean who had trouble tearing his eyes away from the hard flesh sliding beneath his fingers. Benny rewarded Dean’s attention with a harsh, biting kiss. After a long moment, he pulled away from Dean, panting.

“Get under him, cher. Wanna see those lips of yours wrapped around his pretty little cock.” Benny leaned forward again, nipping at Dean’s lips and smiling darkly at the glazed, excited look in Dean’s eyes. Dean stood quickly, stripping off his pants before approaching the bed.

Benny slapped Castiel’s ass before wrapping his free arm around him and pushing up on his chest to make him arch. Dean quickly slipped beneath Castiel, face nosing at Castiel’s straining erection.

“There you go, darling, Dean’s gonna make you feel so good,” Benny cooed, curling his finger to teasingly brush over Castiel’s prostate, causing the smaller man to arch, smearing his oiled cock across Dean’s face. Dean groaned, reaching up quickly to guide Castiel’s cock into his eager mouth. A deep, guttural moan tore from Castiel’s chest. 

Benny leaned down, wagging a finger at the enthusiastically sucking Dean. “Don’t you make that boy come, Dean, or it’ll be your ass.” Dean smirked around the cock stretching his full, pink lips, never releasing the suction as he tongued Castiel’s slit. Dean closed his eyes, face blissed as he continued to suckle and tease at the head.

Benny’s eyes narrowed and he shook his head, adding a second finger and crooking them hard into Castiel’s prostate. Castiel’s belly coiled as he panted, balls pulling up tight signaling his impending orgasm. 

“D-De..” he whined low in his throat, the only warning he was able to give before he suddenly cried out, coming hard down Dean’s throat. Benny milked he through it, swirling his fingers against his prostate even as Dean continued to suckle until Castiel writhed, babbling incoherently, oversensitized to the point of pain. He tried desperately to buck them off, pulling himself from Dean’s wet lips with an obscene pop.

Dean looked up at Benny with wide, innocent eyes from his position between Castiel’s legs, a dribbled bit of come coating his chin. 

Benny arched an eyebrow. “Well?”

Dean’s grinned wickedly and he arched up to lap at the tip even as Castiel pulled away. He smiled smugly. “Mmm, Benny,” Dean purred, his hands running up Castiel’s tense thighs. “He tasted so good. I can’t wait to fuck into his loose, sloppy hole.”

Benny scowled, growling deep in his chest, even snarling as he roughly yanked his fingers Castiel’s puffy hole, causing the smaller man to cry out. Benny rounded the bed, reaching out to loosen only the knot tying Castiel to the headboard before yanking a surprised Dean out from underneath him. 

Startled, Castiel sat up, wincing at the twinge in his ass even as Benny tossed Dean back on the bed, Dean’s head now at the headboard, and lashed his wrists to either side. Benny glared down at the wide-eyed Dean, pinning Dean with a big hand to his chest before giving Dean’s cock a few hard slaps. Dean thrashed, broken cries morphing into panting moans. 

Benny shook a finger at a glassy-eyed Dean. “I warned you, cher. Now you ain’t even get to touch while I fuck ‘im open.”

Dean groaned and Benny resumed kneeling behind Castiel, oiling up his fingers and quickly shoving three into Castiel’s stretched hole. Whining at the burn, Castiel tipped forward, pressing his face to Dean’s thigh and puffing hot breath across Dean’s straining cock. 

Lifting his leg, Dean nudged Castiel’s face closer to the purpled flesh.

“Put that mouth to use, boy.” Dean thrust his hips shallowly, dragging his cock across Castiel’s open mouth. His grin turned feral when Castiel closed his lips around Dean’s cock, sucking gently. “That’s it,” Dean growled, thrusts becoming deeper. “Suck my cock.”

Castiel yelped, releasing Dean’s spit covered cock, and arching up as Benny yanked his hair hard. Benny’s hard chest pressed against his back and Castiel gasped when he felt the blunt head of Benny’s oiled cock just breaching his rim.

“Now, now, Dean,” Benny barked, leaning around Castiel to give Dean’s cock another hard slap. “You only get what I give you.” 

Dean whined, jerking his hips away from the stinging slaps. He winced but his eyes never left Benny’s as the bear of a man straightened up before snapping his hips forward and sheathing himself inside Castiel who tensed and screamed. Benny smirked, shoving Castiel down, pressing his panting face to Dean’s crotch. He reached under Castiel, snaking his arms up his chest and wrapping his big hands around Castiel’s shoulders. 

“Ready, darling?” he drawled, not waiting for an answer as be using his leverage to begin pounding into Castiel. Dean whined and Castiel moaned, the burning lighting up Castiel’s insides, filling his cock with blood until he ached. 

Behind him, Benny cooed, talking just as much for Dean as he was for Castiel. “Tha’s right, darling. So tight for me. You whine so pretty. Go on, boy. Let the Captain know what he’s missing.”

Dean groaned, thrusting uselessly as Benny continued his bruising pace. 

The rough slap of skin echoed throughout the small space. Castiel whimpered and moaned, Benny panting harshly against his shoulders. Through it all, Dean watched, biting his lip raw and squirming in his distress. Benny adjusted, nailing Castiel’s prostate. Castiel wailed and Dean broke.

“ _Please_ ,” he whimpered, eyes wide and yearning. “Please, Benny.” He began to strain in earnest against his binds, reaching ineffectively with splayed fingers. “ _Benny_ ,” Dean breathed like a prayer, his voice absolutely wrecked. “Want him, Benny. Want you. Please. Let me fill him up.” Dean gasped a choked sob, his eyes wet with frustration. “ _Please_.” 

Easing up his pace, Benny mouthed the back of Castiel’s neck. “How bout it, darling?” He panted hotly. “You wanna ride the Captain’s cock? Make him come in your tight little hole?”

Whining, Castiel staring down at Dean’s look of desperation, and nodded.

Castiel winced when Benny eased from his abused hole. Reaching behind him to the floor, Benny coated his fingers in the oil, fisting over Dean’s cock with a few quick strokes and leaving Dean gasping and thrusting at air. He then scooped up more, gently working it into Castiel’s puffy, red rim. With his free hand, Benny tapped the intricate knot work lacing up Castiel’s forearms. 

“If I untie you, darling, you promise to be so good for me?”

Castiel nodded. He watched in awe as with a few tugs Benny managed to single-handedly unravel all he’d done before.

Pulling his slick fingers from Castiel’s ass, Benny stood up on the bed, pulling Castiel with him. He arranged Castiel, having him turn his back toward the Captain before placing his feet on either side of his thighs and helping him to squat until Castiel pierced himself on Dean’s hard cock. Both men sigh in unison as Castiel sank slowly down, seating himself firmly in Dean’s lap. Leaning forward slightly, Castiel braced himself on Dean’s knees, bouncing experimentally and groaning when Dean’s cockhead grazed along his prostate. Dean threw his head back as Castiel started bouncing in earnest.

Benny smirked, stepping in front of Castiel and fisting a big hand into his dark hair. 

“Tha’s it. Come on, boy. Bet those lips can still suck while you ride.” Castiel offered no resistance as Benny guided his fat cock past his panting lips. Castiel sucked it down eagerly, grinding hard on Dean until with a startled yell, he again, splashing the sheets and dribbling down to run over Dean’s tight balls. The fluttering of Castiel’s tight walls pulled Dean over the edge and he cried out as he emptied himself into Castiel. 

Pulling back, Benny hardly waited for Dean to finish before he yanked Castiel off Dean’s cock, only to flip him over so he knelt next to Dean on the bed, ass in the air. 

“What..” Castiel asked, turning to look only be speared once more by Benny’s talented tongue licking deep over his sensitive walls. Castiel quaked at the onslaught. 

Benny moaned, making the most obscene sounds as he continued to lick Dean’s come from Castiel’s body. Castiel yelped, surprised, when Benny suddenly pushed him out of the way, lunging forward to straddle Dean’s chest and feeding his thick cock into Dean’s waiting mouth. He thrust hard, fucking into Dean’s face, hands fisting Dean’s hair until with a shuddering roar he poured himself down Dean’s throat. 

He eased back, body trembling, and reached out to release Dean from his clever knots. Dean’s hands were on him in an instant, petting and caressing, easing Benny down until he slid boneless next to Dean on the bed. Dean rolled into Benny, peppering his face with soft, chaste kisses while Benny’s breathing slowly returned to normal. 

Sighing deeply, Benny returned a sweet kiss to Dean’s lips before sitting up with a groan. He ran a hand through his short hair and turned to regard the two men sharing the bed. He reached over Dean to pat Castiel’s thigh. 

“Wash up, No time for sleep. Captain, cher, you need to make an appearance with the crew.”

Dean groaned but nodded, propping himself up on an elbow. He threw a smirk at Castiel. “Might as well introduce them all to our new cabin boy.” He turned a critical gaze on Benny. “You’ll make sure Raphael and Lucifer know to keep their filthy hands off?”

“Aye.”

Benny stood, picking his and Castiel’s breeches from the floor. He tossed Castiel’s to him before pulling his on with quick, efficient movements. 

“Up with you, boy. There’s work to be done.”

They all dressed in relative silence, Benny only pausing to help Dean ease into his jacket before gripping the lapels to pull the Captain in for a filthy kiss. 

Dean grinned roguishly and turned on his heel. “Let’s get to it.” 

Castiel winced when Dean slapped his ass as he breezed by. Pulling open the door, he stepped through, Benny following just behind and a nervous, slightly limping Castiel bring up the rear.

**Author's Note:**

> [Tumblr! Tumblr! Oi! Oi! Oi!](http://emani-writes.tumblr.com/)


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